Hopeless
by Little Purple Bunny
Summary: Drew loves May but is totally hopeless with girls. He decides to ask Dawn, May's best friend, for help. They come up with a plan but it doesn't seem to go as well as planned...


_Hello =D_

_So this is my first Contestshipping fic, no wait-first one-shot...Actually, it's my first fanfic :P Well no wait, actually (LOL) it's not exactly my first since I've written some others before but it is the first posted on this website! :D _

_Disclaimer: I do not own Pokemon D=_

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**Hopeless  
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I was just an ordinary teenager…with hormones. Okay I added that last part because I had a crush on someone. That someone was well…um well, May. I met her when I was 10, we never really got along. Whenever we talked, I always ended up being mean or teasing her. Therefore, she never really wanted to hang out with me.

I liked her. No scratch that- I loved her. I don't know why but I always ended up being mean to her, I guess I was just bad with girls. I did try to be good by giving her roses though!

Now you're probably wondering who I am.

Well that, is a secret.

"DREW!"

Damn...

There goes my secret.

"What do you want to ask me?" Dawn tilted her head to the side, looking confused. Oh right! I was asking her for help.

"Dawn," I took a deep breath, wondering how she would take it, "I like May."

Dawn raised an eyebrow, "And you're telling me this...why?"

She obviously thought I was confessing to the wrong person or something, "Well you're her best friend and I thought you would be able to help me to get her to like me." I suggested, shyly.

Dawn laughed at me, "I'm sorry but are you serious?"

"What do you mean am I serious?" I asked out of annoyance. Of course I was! Did I really have to repeat myself?

"Well for one, you make fun of her constantly! Two, you make her so down! Three, you make her feel like crap!" Dawn yelled at me, looking annoyed. Wow…I mean I knew I was mean to her but that made me think I was an even more mean person to her than what I originally thought.

I sighed at her, "I know, I'm awful with girls!"

"Yeah you really suck at trying to get a girl to like you," Dawn muttered under her breath. Oh that _hurt_…

I rolled my eyes, "So can you help?"

Dawn glared at me, this was not good…"Alright but let me get this straight first, you treat May like dirt, make her down, even tease her about her contest skills_, _insult her every chance you get and now you want me to set you up with May?"

I nodded slowly, yeah pretty much.

"Soo…" Dawn paused, looking at me directly to my eyes with a glare, "No."

I frowned, "Please? I'm using the magic word here!"

"I don't know if she wants me to do that," Dawn told me, irritated, "I mean, after all you've done…she'd be furious at me for setting you up!"

"But…" I didn't know what to do, I decided to do my best puppy dog face, "If you don't, I'll keep this up until you help me."

"Fine I'll help you!" Dawn groaned, "First, I'll tell you about her."

I smirked and flipped my hair, it worked! "Sure, so what is there to know about?" I asked.

"Well for starters, she's easy to upset," Dawn grinned at me, "You probably already knew that."

"I get it! I'm a bad person, stop rubbing that in my face! Tell me something I don't know." I groaned, frowning at her.

"Okay," Dawn continued, "She's good with her Pokemon, she doesn't think she is because you insult her about it. Although, she never gives up."

I continued to frown, so I was the reason why she doubted herself? "You know…I actually think her coordinating skills are pretty awesome," I brightened myself up, it was true, I really did think so.

Dawn gasped, then scowled, "Are you serious? Then why do you tell her she sucks?" She yelled at me, frustrated, "Why don't you just tell her the truth?"

I fell in silence, thinking about what she just said. I insulted her a lot and I didn't know why! I just did…"I-I can't!"

"Why?" She glared, "I can't be your messenger! I mean what am I supposed to say, 'Hey May, Drew likes you even though he's mean to you, you should totally date him!' " She mocked.

I rolled my eyes, "Alright I guess that's not going to work…" I sighed sadly, then something hit me, "Hey I've got an idea!"

"Alright, tell me."

"Well you and May can start a conversation in the park around 10 o'clock, talk about gossip and make-up, whatever you girls talk about. Then later I come in, you will say you have to go but really you are eavesdropping on us behind a tree. I will continue the chat with May and I will be extra nice to her!" I grinned proudly at my plan.

Dawn, on the other hand, was deep in thought about it, she finally opened her mouth, "Yeah but I don't think you'll be saying the right things." She mumbled.

I knew I was hopeless when talking with girls, "Hm yeah…"

"I know! Whenever you say something wrong, I get to throw a rock at you." Dawn beamed at her idea.

I nodded and smirked, "Great! Our plans are sorted! See ya tomorrow!"

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Today was going to be terrible, I just had a feeling. Although, I had to hope for the best! Plan GMTLD 1# was what Dawn and I had named it. It stood for 'Plan: Get May To Love Drew Attempt 1' We added Attempt 1 in case there were more tries.

I was at the park.

I hid behind a tree and checked the time, 10 o'clock. Dawn should be here with May, she was trying to get her to come to the park.

I spotted Dawn and May coming over, Dawn glanced over at me and quickly said something. Then ran off to me leaving May sitting at a bench by herself.

"Okay I got her here!" Dawn whispered to me quickly, "I'll talk to her, then when I go, you step in! Got that?"

I nodded and Dawn ran back.

They were sitting on a bench together talking about things, luckily I could eavesdrop on them since the tree was pretty close.

"Why were you talking to the tree, Dawn?" May asked, looking confused. Oh so she saw…

Dawn was trying to lie, "Err uhh…" I guess it was hard to find an excuse for talking to a 'tree' well really, it was me, "I wasn't talking! I was just moving my mouth, it's a hobby of mine!"

May was even more confused. I laughed mentally in my head at Dawn's bad lie, "Then why did you go to the tree and come back? What was the point of that?"

"I thought I saw a dead bird on the ground!" Dawn lied again, much quicker than last time.

May smiled, completely understanding, I can't believe she actually believed that! "Oh I see."

"Well I got to go do some stuff!" Dawn got up from her chair, and waved, "Bye May!"

May waved back, "If you're going to go so soon, why did you force me to come here?"

"The weather was nice!" Dawn exclaimed and walked away, when she reached the tree, she quickly went behind it and gave me a thumbs up.

I nodded and knew it was my turn, luckily May wasn't looking at the tree of where Dawn went.

Here goes nothing…

"Um hey May!" I greeted, flipping my hair as I showed myself in front of her.

She didn't look too happy to see me, "Oh hi."

"So…" Well this was awkward, "So…um, how are you?" Completely not the best way to start a conversation but…whatever.

"Fine." She said, flat out. I was trying to start a conversation here, and she answered me with a one word answer? Great…just great.

Then I noticed she had her Beautifly beside her, it was a beautiful Pokemon. I gave her roses but I always said it was for Beautifly. I mean giving a rose to a girl is awkward, you had to think of an excuse!

"Is Beautifly going to be in your next contest?" I asked, it was good to start a conversation! "I mean, you're amazing with contests."

May looked at me with a puzzled face, maybe because I was complimenting her for a change, "Uh sure, but I thought you thought I was bad."

"I do," I said instantly, contradicting myself. I mentally slapped myself for saying that, why couldn't I think before I spoke? "Ow!" I felt a pebble hitting me, "I mean you're not too ba-OW! I mean you're awesome."

I was so hopeless.

"Oh thanks…I guess," May raised an eyebrow. "The other day…" Wow, she was actually starting the conversation! Maybe she was opening up to me? That's a good sign!

"Yeah?"

"Ash was watching me in a contest battle and he said I was going to be one of the best coordinators in the region," May grinned proudly, "He said I was really good."

"Ash, aye?" I questioned, I think I was getting jealous. I could practically feel the steam coming out of my ears, "OW!" A pebble immediately hit me. Yeah, that was probably for my jealousy.

May gave a questioning look, the nodded, "He even said I inspired him to enter another contest!" I really couldn't help my jealousy.

"He obviously doesn't know good coordinating skills when you see it," I replied angrily, oops, what I just said to her was not true, I expected a pebble to be thrown at me again…and I was right, "OW! I mean you really are good. He's right."

"Really? I'll show you a move Beautifly can do!" May beamed, I had to make sure I wouldn't insult her like I always did.

May shouted, "Beautifly! Gust attack!" Beautifly began flapping her wings to create a huge wind that was really strong that even I could feel it! My hair began to mess up. Ugh, I spent like 30 minutes on it this morning! "Yeah I know you dislike it..."

"Yeah I do, it ruined my hair! Ow! I mean I think you should show me more moves some other time instead of hanging out with Ash- OW! Ow! Ow!"

May looked very lost.

I took the time to try and fix my hair.

She asked me slowly, "Why do you keep saying ow?"

"I keep hitting myself on the bench," I lied quickly, she really couldn't know about the pebbles. I sighed and decided to give up on this, "I um, I have to go to the restroom."

As soon as I said that, I got up and she began training her Beautifly.

I walked over to behind the tree to meet up with Dawn, she sighed at me, "That was terrible!"

I rolled my eyes, "I give up!" I groaned, "I'm awful with girls!"

"When you said you were awful, I believed you meant you were shy or something but you really are awful," Dawn told me. Gee thanks.

"I know…Plan GMTLD 1# is a total fail," I responded sadly.

Dawn nodded, "Yeah I guess, I'll go back in and try to talk her through it." I didn't exactly know what she was talking about but I shrugged, hoping it meant something good. She walked away from behind the tree and to May.

It was now my turn again to eavesdrop.

"May!" Dawn called out her name which caused May to look up straight away. She seemed happier to see her than with me.

May beamed, "Hey Dawn, Drew was just with me." So she was talking about me? Was that good?

Dawn put on an act, "Oh really? How was it?" She asked, "Was he being mean? Was he nice?"

"He was acting really weird," May answered, scrunching up her face, "Like he wasn't being mean but he wasn't being nice either. He kept on saying ow!"

Dawn looked at her, putting on a strange face, "He wasn't supposed to act weird."

May looked puzzled, "And what do you mean by supposed?"

Oh no…Dawn then blurted something that I really didn't want to happen. Oh dear...it was NOT part of the plan!

"Drew loves you."

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_A/N: End! :3 Yeah I just left it like that xD I planned this to be a one-shot and then when I got to the end, I had trouble with it :P So I'll just leave it like that :) Pretend that May loves him back and they live happily ever after... Or if that doesn't work, I may continue this but I actually haven't planned the next chapters so probably not._

_Okay about the story, I chose Dawn to be May's best friend because I couldn't think of anyone so lets just pretend their in the same region. Oh and I chose Ash to be the person that Drew is jealous of because Brendan (Who is usually that guy) isn't in the anime. I didn't want it to be AU :P It kind of is AU though xDD_

_I hope I didn't do too bad :\ Please tell me what you thought of it by reviewing! I'd love to hear your opinions ;)  
Please tell me if there are any spelling errors or grammar mistakes (I just went through and had to fix some sentences)_

_Well, have a nice day! Take care~_


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